6342-87-6
6342-87-6 结构式
基本信息
2,3-二氢-1H-环戊烷并[A]萘-1-酮
2,3-二氢-1H-环戊二烯并[A]萘-1-酮
1H-Benz[e]inden-1-one, 2,3-dihydro-
2,3-DIHYDRO-CYCLOPENTA[A]NAPHTHALEN-1-ONE
2,3-Dihydro-1H-cyclopenta[a]naphthalen-1-one
物理化学性质
制备方法
21658-35-5
6342-87-6
在装有机械搅拌器的烧瓶中，于室温下分批加入144.0 g P4O10和840 mL甲磺酸制备的Eaton试剂。随后，向该体系中加入144.0 g（约720 mmol）3-(2-萘基)丙酸。将反应混合物搅拌过夜后，缓慢倒入2 L冰冷的水中淬灭反应。用3×500 mL二氯甲烷萃取粗产物，合并有机相。有机相依次用K2CO3水溶液洗涤，无水Na2SO4干燥，减压浓缩至干。残余物通过快速柱色谱纯化，使用600 mL硅胶60（40-63 μm）作为固定相，己烷与二氯甲烷（1:1，v/v）作为洗脱剂，得到105.0 g（产率80%）目标化合物2,3-二氢-1H-苯并[e]茚-1-酮，为褐色固体。元素分析（C13H10O）计算值：C, 85.69; H, 5.53。实测值：C, 85.98; H, 5.75。1H NMR (CDCl3) δ: 9.12 (d, J = 8.5 Hz, 1H), 7.93 (d, J = 8.3 Hz, 1H), 7.81 (d, J = 8.1 Hz, 1H), 7.61 (ddd, J = 8.3, 7.1, 1.2 Hz, 1H), 7.50 (ddd, J = 8.1, 7.1, 1.0 Hz, 1H), 7.39 (d, J = 8.3 Hz, 1H), 3.12-3.04 (m, 2H), 2.75-2.65 (m, 2H)。13C{1H} NMR (CDCl3) δ: 207.26, 158.26, 135.47, 132.41, 130.81, 129.23, 128.65, 127.90, 126.39, 123.87, 123.76, 36.73, 25.99。
参考文献：
[1] Journal of the American Chemical Society, 2001, vol. 123, # 14, p. 3214 - 3222
[2] Chemistry - A European Journal, 2015, vol. 21, # 37, p. 13052 - 13057
[3] Patent: WO2017/118617, 2017, A1. Location in patent: Page/Page column 20
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1985, p. 1845 - 1848
[5] Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 1983, vol. 22, # 10, p. 1015 - 1019